
Holiday rentals with a pool in Chesil Beach
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Chesil Beach
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

Headland Hideaway Shepherd's Hut in Lyme Regis
SHEPHERDS HUT An opulent hideaway retreat nestled on the Lyme Bay headland with uninterrupted ocean views, perfect for romantics & family adventurers. With an expansive sundeck, fire pit & swimming pool & endless expanse of garden. Embark on the most charming private adventure from bedroom shepherd's hut & adjacent shower room to the architectural wonder of the glass framed kitchen, diner & sitting room with freestanding log burner & stylish interior. Sit and wonder at the expanse of ocean views

Country House - Pool Jacuzzi Escape Room Karaoke
Group Gatherings Host your own event Exclusive use 10-16 guests Min 2 off peak Jacuzzi All year Outdoor Pool (heated in summer; cold in winter!) Sun Deck Garden Kitchen/Bar Games room: Music/Karaoke system Wood burner TV Communal eating space, shower/wc Escape Room Somerset Evening -pulled pork cider tasting welly wanging Large peaceful grounds BBQ Fire Pit Annexe (sole use) kitchen lounge bathroom 2 bedrooms 2 sofa beds House (part use): 4 bedrooms 3 bathrooms Glamping Trailer

Luxury House 100m to beach - sleeps 8 Pool+Hot Tub
This stylish place to stay is perfect for family trips. A short stroll to the beaches and harbour at West Bay makes the house the perfect location for a beach holiday. The South West Coast Path and Jurassic Coast are just 25 metres from the door. A heated swim spa and separate hot tub are among the many facilities at the house. Ample private parking includes 2 EV Chargers. Spectacular views across Lyme Bay to Portland. Beautiful bathrooms and Showers. Luxury Kitchen. Wonderful terraces and BBQ.

Kingfisher yurt, A unique eco holiday in Devon
Unique yurt (sleeps 5+) surrounded by oak trees, next to the wild swimming pond (shared /gated.) Also check out Buzzard yurt with its terrace / views Private large, rustic, open plan kitchen (+ games, maps and books), shower, compost loo and fire pit. The shared games/music cabin adjoins your kitchen. Dog friendly. Use of our 26 acre rewilding woodland a 45 minute hike away. Bookable hot tub. The safety of your group is your responsibility. Check-in form /waiver to sign on arrival please.

Everdene shepherd's hut
Lovely views of the Blackmore Vale (amazing sunsets weather permitting!) Our huts are in a secluded area of the farm. Kingsize bed/twin beds opposite ends with curtains for privacy. Woodburner, hot/cold running water, fridge, hob, microwave, wardrobe. Picnic bench & fire pit outside. Wonderful walks, only 10 minutes on foot to village shop and pub. Great for families. Short walk to luxury wetrooms, w/m, drier. Fishing on farm. Indoor exercise pool payable locally. (Subject to availability)

A luxury unique home spa - White Stones Retreats.
Set in a prime position amidst a quintessential village of thatched cottages. Where wildflower paths and trickling streams amble down the the beautiful Osmington Bay. Toe dipping in the shallows, coastal walks under flaring sunsets, hibernating in our home spa while storms crash outside. Our unique holiday home offers a sanctuary in all weathers. With a collated & collected vibe, this light filled cottage is perfect for families looking for a beach escape, only a 5 minute drive to the sea.

Secluded hideaway, heated pool, walks, fossils
The Annex is bright, comfortable and cosy with a wood burner for winter. The public footpath crossing our garden next to the river Char links with many others - great for dog walkers. We are close to Charmouth beach and Lyme Regis – renowned for their fossil treasures. Love swimming? our freshwater pool is generally heated to a very cosy 29 - 30 degrees (warm bath temperature) and can be used from April to October With advance notice, the twin beds can be connected to form a king size bed

Clover Carriage with pool, sauna and outdoor bath
Nestled into our working farm, this lovingly restored railway carriage is the perfect spot for a romantic stay away. The views are out of this world and all viewable from the large glass doors so you can stay tucked up in bed or on the sofa in front of the fire, with great wifi, free access to our beautiful heate pool & sauna (located in the pool house), beautiful walks both from the carriage or a short drive to the coast path, pub lunches, sunsets, fairy lights and a romantic outdoor bath

Spacious Caravan near sea Weymouth Bay Haven
Our holiday home is spacious with a well equipped kitchen. Located 12-15min flat walk (buggy friendly) from the seaside. The Haven park offers a swimming pool, live entertainment and play areas for kids until 14th November (access to indoor complex is an additional fee on a first come first serve basis) We are opposite the activity field. One car parking space next to the caravan.. CHANGEOVER DAYS ARE MONDAY OR FRIDAY. Please contact us to make a shorter booking or with any questions.

Daisy Cottage on the Jurassic Coast
A cosy and stylish, dog-friendly cottage, set amid the beautiful fields and woodlands of the Fernhill Estate with easy walking access to the coastal village of Charmouth and only 2 miles to Lyme Regis. The South West Coastal Path runs opposite our front door and our guests have seasonal access to a heated outdoor pool. Our cottage sleeps four and is furnished and equipped to a very high standard with everything you need for a relaxing holiday on the Jurassic Coast in West Dorset.

The Duck House. A child/dog friendly rural chalet
The Duck House is a lovely child/dog friendly chalet nestling in the orchard at Plenty Cottage. Quiet and peaceful it's the perfect retreat for a family - and dogs are especially welcome! Open plan living it’s a comfortable and home from home. A wonderful rambling garden, summerhouse, BBQ and a (free) heated swimming pool (1st April - 31st Sept). The mantra is 'No Stress'. Ample parking, dog/child friendly pub 7 mins walk away. Wonderful NT beaches just five min drive.

The Condo (Indoor Pool available May- end Sept)
Self contained detached cottage in a tranquil location close to the famous 'Jurassic Coast' ; Durdle Door, Lulworth, Corfe Castle, Weymouth and Dorchester are all a short drive away. Further attractions close by are Monkey World, Bovington Tank Museum, and Sculpture by the lakes. There is a well stocked village shop and good village pub. Dorset has so much to offer, with beautiful coastline and breathtaking scenery. Relax in the pool at your leisure!
Popular amenities for Chesil Beach rentals with a pool
House rentals with a pool

Stunning Home with Roof Terrace at Silverlake

Your Own Private Indoor Pool. Rural Seaside

Charming thatched farmhouse, heated pool & cottage

Large Airy Barn conversion, 5 bedrooms, Jurassic

East Creek + beach side + pool, dog Ringstead Bay

Flint Cottage for two with indoor pool & sauna

Peaceful West Dorset location

The Lighthouse (BR03), Silverlake, Dorset
Other holiday rentals with a pool

3 Bed in Folke (FOLWR)

Stunning Barn conversion with heated swimming pool

Beautiful 6 berth static caravan

Warmwell Luxury Lodge near Weymouth with Pool

A homely seaside static caravan

Somerset | Festive Stays Frm £5k

Kingfisher Lodge with Sea Views

Donkey Lovers Retreat
Destinations to explore
- Paris Holiday rentals
- London Holiday rentals
- Picardy Holiday rentals
- Grand Paris Holiday rentals
- Thames River Holiday rentals
- South West England Holiday rentals
- Inner London Holiday rentals
- Rivière Holiday rentals
- Dublin Holiday rentals
- South London Holiday rentals
- Central London Holiday rentals
- Yorkshire Holiday rentals
- Rentals with an EV charger Chesil Beach
- Rentals with a hot tub Chesil Beach
- Rentals with a firepit Chesil Beach
- Rentals with lake access Chesil Beach
- Rentals with a fireplace Chesil Beach
- Rentals with beach access Chesil Beach
- Family-friendly rentals Chesil Beach
- Waterfront rentals Chesil Beach
- Fitness-friendly rentals Chesil Beach
- Flat rentals Chesil Beach
- Beachfront rentals Chesil Beach
- Hotel rentals Chesil Beach
- Rentals with a washing machine and dryer Chesil Beach
- House rentals Chesil Beach
- Private suite rentals Chesil Beach
- Cottage rentals Chesil Beach
- Pet-friendly rentals Chesil Beach
- Bed and breakfasts Chesil Beach
- Rentals with breakfast Chesil Beach
- Rentals with a patio Chesil Beach
- Townhouse rentals Chesil Beach
- Guest house rentals Chesil Beach
- Apartment rentals Chesil Beach
- Rentals with outdoor seating Chesil Beach
- Rentals with pools England
- Rentals with pools United Kingdom
- New Forest national park
- Paultons Park Home of Peppa Pig World
- Weymouth Beach
- Bournemouth Beach
- Stonehenge
- Boscombe Beach
- Kimmeridge Bay
- Southbourne Beach
- Highcliffe Beach
- The Tank Museum
- Poole Quay
- Crealy Theme Park & Resort
- Sandy Bay Beach Blue Flag Winner 2019
- Preston Sands
- Beer Beach
- Mudeford Sandbank
- Man O'War Beach
- Charmouth Beach
- Torre Abbey
- Oddicombe Beach
- Dartmouth Castle
- Oake Manor Golf Club
- Hurst Castle
- Compton Beach